Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones

Abstract

Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones, processes for their preparation, fungicidal compositions containing them and methods of using them to treat or prevent fungal disease in crops.

What is claimed is: 
     
       1. A compound having the formula: ##STR84## or an agriculturally acceptable salt thereof, wherein: W is S, O or S═O; each of R 1  and R 2 , which are identical or different, is: H, provided that one of R 1  and R 2  is different from H;   alkyl or haloalkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or alkynyl having 2 to 6 carbon atoms;   dialkylaminoalkyl or cycloalkyl having 3 to 7 carbon atoms;   aryl selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; or   arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl, wherein alkyl has 1 to 6 carbon atoms and aryl is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   or R 1  and R 2  taken together form, with the carbon to which they are bonded on the ring, a carbocyclic ring having from 5 to 7 atoms, or a carbocyclic ring having from 5 to 7 atoms which is fused to a phenyl ring which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;     R 3  is: alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl having 2 to 6 carbon atoms;   dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl having 3 to 6 carbon atoms;   N,N-dialkylcarbamoylalkyl having 4 to 8 carbon atoms; or   arylalkyl, the alkyl portion having 1 to 6 carbon atoms and the aryl portion being phenyl, naphthyl, thienyl, furyl or pyridyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;     R 4  is: hydrogen, provided that n is other than zero;   alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl having 2 to 6 carbon atoms;   dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl having 3 to 6 carbon atoms;   N,N-dialkylcarbamoylalkyl having 4 to 8 carbon atoms;   aryl selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl, wherein alkyl has 1 to 6 carbon atoms and aryl is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   amino, disubstituted by 2 identical or different substituents selected from the group consisting of: alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   cycloalkyl having 3 to 7 carbon atoms;   arylalkyl as defined above for R 4 , phenyl and naphthyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; and   thienylmethyl and furfuryl; or     pyrrolidino, piperidino, morpholino or piperazino, each of which is unsubstituted or is substituted by alkyl having 1 to 3 carbon atoms;     R 5  is: H, provided that R 4  is other than H;   alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkylsulfonyl or cyanoalkylsulfonyl having 2 to 6 carbon atoms;   alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl having 3 to 6 carbon atoms;   formyl;   cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoacyl, alkenylcarbonyl or alkynylcarbonyl having 3 to 6 carbon atoms;   cycloalkylcarbonyl having 4 to 8 carbon atoms;   phenyl; phenylalkylcarbonyl wherein the alkyl portion has 1 to 6 carbon atoms; benzoyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio)carbonyl, the phenyl portion of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; (alkylthio)carbonyl, (haloalkylthio)carbonyl, (alkoxyalkylthio)carbonyl or (cyanoalkylthio)carbonyl, the alkyl and alkoxy portions of which each has 1 to 6 carbon atoms; (benzylthio)carbonyl; (furfurylthio)carbonyl; (tetrahydrofurfurylthio)carbonyl; (thienylmethylthio)carbonyl; (pyridylmethylthio)carbonyl; or arylsulfonyl, the aryl portion of which is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   carbamoyl, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of: alkyl and haloalkyl having 1 to 6 carbon atoms;   cycloalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl and cyanoalkyl having 2 to 6 carbon atoms; and   phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;     sulfamoyl, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of: alkyl and haloalkyl having 1 to 6 carbon atoms;   cycloalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl and cyanoalkyl having 2 to 6 carbon atoms; and   phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; or     alkylthioalkylsulfonyl having 3 to 8 carbon atoms or cycloalkylsulfonyl having 3 to 7 carbon atoms; and     R 7  is: halogen;   alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, or alkylsulfonyl having 1 to 6 carbon atoms;   cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynylthio having 3 to 6 carbon atoms;   nitro or cyano;   amino, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of alkyl and acyl having 1 to 6 carbon atoms and alkoxycarbonyl having 2 to 6 carbon atoms; or   phenyl, phenoxy or pyridyloxy, each of which is unsubstituted or is substituted by 1 to 3 substituents selected from the group consisting of halogen and alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio and alkylsulfonyl having 1 to 6 carbon atoms;   with the exclusion of a compound wherein R 1  is hydrogen, each of R 5  and R 4  is methyl, R 3  is methyl, W is O and R 2  is hydrogen, methyl or phenyl.     
     
     
       2. A compound according to claim 1, wherein R 5  is H. 
     
     
       3. A compound according to claim 1, wherein W is O. 
     
     
       4. A compound according to claim 1, wherein R 1  and R 2  are other than H. 
     
     
       5. A compound according to claim 1, wherein R 2  is alkyl having 1 to 3 carbon atoms. 
     
     
       6. A compound according to claim 1, wherein R 1  is phenyl, which is unsubstituted or is substituted by an R 7  substituent wherein R 7  is as defined in claim 5. 
     
     
       7. A compound according to claim 1, wherein R 3  is alkyl having 1 to 3 carbon atoms. 
     
     
       8. A compound according to claim 1, wherein R 4  is phenyl, which is unsubstituted or is substituted by an R 7  substituent wherein R 7  is as defined in claim 1. 
     
     
       9. A compound according to claim 7, wherein R 3  is methyl. 
     
     
       10. A compound according to claim 1, having the formula: ##STR85## wherein W is S, O or S═O; R 2  is CH 3  ; R 3  is methyl, ethyl, propyl or difluoromethyl; R 4  is phenyl, m-tolyl, p-tolyl, 4-fluorophenyl, o-tolyl, 3-chlorophenyl, 4-chlorophenyl, 2-chlorophenyl, 4-methoxyphenyl, 2-methoxyphenyl, 4-nitrophenyl or 2-pyridyl, and R 5  is H, methyl or acetyl. 
     
     
       11. The compound according to claim 10, wherein: W is S, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is H;   W is S═O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is m-tolyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is p-tolyl and R 5  is H;   W is O, R 2  is methyl, R 3  is ethyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 4-fluorophenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is o-tolyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 3-chlorophenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is isopropyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 4-chlorophenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 2-chlorophenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is methyl;   W is O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 4-methoxyphenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is n-propyl, R 4  is phenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 2-methoxyphenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 4-nitrophenyl and R 5  is H;   W is O, R 2  is methyl, R 3  is methyl, R 4  is 2-pyridyl and R 5  is H; or   W is O, R 2  is methyl, R 3  is difluoromethyl, R 4  is phenyl and R 5  is H.   
     
     
       12. The compound according to claim 1, having the formula: ##STR86## wherein: W is O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is formyl; or W is O, R 2  is methyl, R 3  is methyl, R 4  is phenyl and R 5  is t-butoxycarbonyl.   
     
     
       13. A compound according to claim 1, having the formula: ##STR87## wherein W is O; R 2  is methyl or ethyl; R 3  is methyl; R 4  is phenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl or 2-ethylphenyl; and R 5  is H. 
     
     
       14. The compound according to claim 13, wherein: R 2  is ethyl, R 3  is methyl and R 4  is phenyl;   R 2  is methyl, R 3  is methyl and R 4  is 2,4-dimethylphenyl;   R 2  is methyl, R 3  is methyl and R 4  is 2,5-dimethylphenyl; or   R 2  is methyl, R 3  is methyl and R 4  is 2-ethylphenyl.   
     
     
       15. The compound according to claim 1, which is 4-methyl-2-methylthio-4-(4-fluorophenyl)-1-phenylamino-2-imidazolin-5-one. 
     
     
       16. A compound according to claim 1, having the formula: ##STR88## wherein R' 1  is H, 4-methyl, 4-chloro, 4-phenoxy, 4-fluoro or 4-chloro; and R 4  is 2,3-dimethylphenyl, 3-pyridyl, phenyl, 3-methyl-2-pyridyl, 2-methylphenyl, 2-pyridyl, 2-chlorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-methylphenyl, 3-methylphenyl or 3-fluorophenyl. 
     
     
       17. The compound according to claim 16, wherein: R' 1  is H and R 4  is 2,3-dimethylphenyl;   R' 1  is 4-methyl and R 4  is phenyl;   R' 1  is H and R 4  is 3-methyl-2-pyridyl;   R' 1  is 4-chloro and R 4  is phenyl;   R' 1  is 4-methyl and R 4  is 2-methylphenyl;   R' 1  is 4-phenoxy and R 4  is phenyl;   R' 1  is 4-chloro and R 4  is 3-methyl-2-pyridyl;   R' 1  is 4-chloro and R 4  is 2-pyridyl;   R' 1  is 4-phenoxy and R 4  is 2-methylphenyl;   R' 1  is 4-fluoro and R 4  is 2-methylphenyl;   R' 1  is 4-chloro and R 4  is 2-chlorophenyl;   R' 1  is 4-chloro and R 4  is 4-fluorophenyl;   R' 1  is 4-chloro and R 4  is 3-chlorophenyl;   R' 1  is 4-chloro and R 4  is 4-methylphenyl;   R' 1  is 4-chloro and R 4  is 2-methylphenyl;   R' 1  is 4-chloro and R 4  is 3-methylphenyl;   R' 1  is 4-fluoro and R 4  is 3-methylphenyl; or   R' 1  is H and R 4  is 3-fluorophenyl.   
     
     
       18. The compound according to claim 1, having the formula: ##STR89## 
     
     
       19. A compound having the formula: or an agriculturally acceptable salt or optically active isomer thereof, wherein: W is S, O or S═O;   each of R 1  and R 2 , which are identical or different, is: H, provided that one of R 1  and R 2  is different from H;   alkyl or haloalkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, monoalkylaminoalkyl, alkenyl or alkynyl radical having 2 to 6 carbon atoms;   dialkylaminoalkyl or cycloalkyl having 3 to 7 carbon atoms;   aryl selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; or   arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl, wherein alkyl has 1 to 6 carbon atoms and aryl is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   or R 1  and R 2  taken together form, with the carbon to which they are bonded on the ring, a carbocyclic ring having from 5 to 7 atoms, or a carbocyclic or heterocyclic ring having 5 to 7 atoms which is fused to a phenyl ring which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;     R 30  is: hydrogen or alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, alkylsulfonylalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, oxoalkyl, alkenyl or alkynyl having 2 to 6 carbon atoms;   dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl having 3 to 6 carbon atoms; or   N,N-dialkylcarbamoylalkyl having 4 to 8 carbon atoms;     R 40  is: hydrogen;   alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, haloalkyl, cyanoalkyl, thiocyanatoalkyl, alkenyl or alkynyl having 2 to 6 carbon atoms;   dialkylaminoalkyl, alkoxycarbonylalkyl or N-alkylcarbamoylalkyl having 3 to 6 carbon atoms;   N,N-dialkylcarbamoylalkyl having 4 to 8 carbon atoms;   aryl selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   arylalkyl, aryloxyalkyl, arylthioalkyl or arylsulfonylalkyl, wherein alkyl has 1 to 6 carbon atoms and aryl is selected from the group consisting of phenyl, naphthyl, thienyl, furyl, pyridyl, imidazolyl, pyrazolyl, pyrrolyl, triazolyl, pyrimidyl, pyridazinyl, pyrazinyl, benzothienyl, benzofuryl, quinolyl, isoquinolyl and methylenedioxyphenyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;   amino, disubstituted by 2 identical or different substituents selected from the group consisting of: alkyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   cycloalkyl having 3 to 7 carbon atoms;   arylalkyl as defined above for R 40 , phenyl and naphthyl, each of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; and   thienylmethyl and furfuryl; or     pyrrolidino, piperidino, morpholino or piperazino, each of which is unsubstituted or is substituted by alkyl having 1 to 3 carbon atoms;     R 5  is: H, provided that R 40  is other than H;   alkyl, haloalkyl, alkylsulfonyl or haloalkylsulfonyl having 1 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl, acyl, alkenyl, alkynyl, haloacyl, alkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkylsulfonyl or cyanoalkylsulfonyl having 2 to 6 carbon atoms;   alkoxyalkoxycarbonyl, alkylthioalkoxycarbonyl or cyanoalkoxycarbonyl having 3 to 6 carbon atoms;   formyl;   cycloalkyl, alkoxyacyl, alkylthioacyl, cyanoacyl, alkenylcarbonyl or alkynylcarbonyl having 3 to 6 carbon atoms;   cycloalkylcarbonyl having 4 to 8 carbon atoms;   phenyl; phenylalkylcarbonyl; benzoyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; thienylcarbonyl; furylcarbonyl; pyridylcarbonyl; benzyloxycarbonyl; furfuryloxycarbonyl; tetrahydrofurfuryloxycarbonyl; thienylmethoxycarbonyl; pyridylmethoxycarbonyl; phenoxycarbonyl or (phenylthio)carbonyl, the phenyl portion of which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; (alkylthio)carbonyl; (haloalkylthio)carbonyl; (alkoxyalkylthio)carbonyl; (cyanoalkylthio)carbonyl; (benzylthio)carbonyl; (furfurylthio)carbonyl; (tetrahydrofurfurylthio)carbonyl; (thienylmethylthio)carbonyl; (pyridylmethylthio)carbonyl; or arylsulfonyl;   carbamoyl, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of: alkyl and haloalkyl having 1 to 6 carbon atoms;   cycloalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl and cyanoalkyl having 2 to 6 carbon atoms; and   phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below;     sulfamoyl, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of: alkyl and haloalkyl having 1 to 6 carbon atoms;   cycloalkyl, alkenyl and alkynyl having 3 to 6 carbon atoms;   alkoxyalkyl, alkylthioalkyl and cyanoalkyl having 2 to 6 carbon atoms; and   phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; or     alkylthioalkylsulfonyl having 3 to 8 carbon atoms or cycloalkylsulfonyl having 3 to 7 carbon atoms;     R 6  is: hydrogen;   cyano;   alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms;   acyl or alkoxycarbonyl having 2 to 6 carbon atoms; or   benzoyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined below; and     R 7  is: halogen;   alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or alkylsulfonyl having 1 to 6 carbon atoms;   cycloalkyl, halocycloalkyl, alkenyloxy, alkynyloxy, alkenylthio or alkynylthio having 3 to 6 carbon atoms;   nitro or cyano;   amino, which is unsubstituted or is substituted by 1 or 2 substituents selected from the group consisting of alkyl and acyl having 1 to 6 carbon atoms and alkoxycarbonyl having 2 to 6 carbon atoms; or   phenyl, phenoxy or pyridyloxy, each of which is unsubstituted or substituted.     
     
     
       20. A compound according to claim 19, wherein R 5  is hydrogen. 
     
     
       21. A compound according to claim 19, wherein R 1  and R 2  are other than hydrogen. 
     
     
       22. A compound according to claim 19, wherein R 2  is alkyl having 1 to 3 carbon atoms. 
     
     
       23. A compound according to claim 22, wherein R 2  is methyl. 
     
     
       24. A compound according to claim 19, wherein R 1  is phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined in claim 19. 
     
     
       25. A compound according to claim 19, wherein R 30  is alkyl having 1 to 3 carbon atoms, which is unsubstituted or is substituted by one or more halogens, methoxy or methylthio. 
     
     
       26. A compound according to claim 19, wherein R 30  is hydrogen. 
     
     
       27. A compound according to claim 19, wherein R 40  is phenyl, which is unsubstituted or is substituted by 1 to 3 R 7  substituents wherein R 7  is as defined in claim 19. 
     
     
       28. A compound according to claim 19, wherein W is O. 
     
     
       29. The compound according to claim 19, having the formula: ##STR90## wherein: R 1  is phenyl, R 30  is methyl and R 40  is phenyl; R 1  is phenyl, R 30  is ethyl and R 40  is phenyl;   R 1  is phenyl, R 30  is trifluoromethyl and R 40  is phenyl;   R 1  is phenyl, R 30  is trichloromethyl and R 40  is phenyl;   R 1  is phenyl, R 30  is n-propyl and R 40  is phenyl;   R 1  is phenyl, R 30  is isopropyl and R 40  is phenyl;   R 1  is phenyl, R 30  is t-butyl and R 40  is phenyl;   R 1  is 4-chlorophenyl, R 30  is methyl and R 40  is phenyl;   R 1  is 4-chlorophenyl, R 30  is methyl and R 40  is 2-methylphenyl;   R 1  is phenyl, R 30  is chloromethyl and R 40  is phenyl.   
     
     
       30. The compound according to claim 10, having the formula ##STR91## 
     
     
       31. A fungicidal composition comprising: (a) a fungicidally effective amount of a compound of formula (Ib) according to claim 1; and (b) at least one member selected from the group consisting of an agriculturally acceptable solid or liquid vehicle and an agriculturally acceptable surface-active agent.   
     
     
       32. A fungicidal composition according to claim 31, comprising from about 0.5% to about 95% by weight of compound of formula (Ib). 
     
     
       33. A method for the treatment or prevention of fungal disease in crops, said method comprising applying to said crops or to the area in which they grow a fungicidally effective amount of a compound of formula (Ib) according to claim 1. 
     
     
       34. A method for the treatment or prevention of fungal disease in crops, said method comprising applying to said crops or to the area in which they grow a fungicidally effective amount of a composition according to claim 31. 
     
     
       35. A method according to claim 33, comprising applying between about 0.005 and 5 kg/ha of compound of formula (Ib). 
     
     
       36. A method according to claim 35, comprising applying between about 0.01 and 1 kg/ha of compound of formula (Ib). 
     
     
       37. A fungicidal composition comprising: (a) a fungicidally effective amount of a compound of formula (I'a) according to claim 19; and   (b) at least one member selected from the group consisting of an agriculturally acceptable solid or liquid vehicle and an agriculturally acceptable surface-active agent.   
     
     
       38. A fungicidal composition according to claim 27, comprising from about 0.05% to about 95% by weight of compound of formula (I'a). 
     
     
       39. A method for the treatment or prevention of fungal disease in crops, said method comprising applying to said crops or to the area in which they grow a fungicidally effective amount of a compound of formula (I'a) according to claim 19. 
     
     
       40. A method for the treatment or prevention of fungal disease in crops, said method comprising applying to said crops or to the area in which they grow a fungicidally effective amount of a composition according to claim 37. 
     
     
       41. A method according to claim 39, comprising applying between about 0.005 and 5 kg/ha of compound of formula (I'a). 
     
     
       42. A method according to claim 41, comprising applying between about 0.01 and 1 kg/ha of compound of formula (I'a).